反应详情

温度

0 °C

1.432 ml (2.12 g, 0.0185 mol) of methanesulfonyl chloride was added dropwise to a solution of 2 g of 4-phenoxybut-2-yn-1-ol and 2.77 ml of triethylamine in 30 ml of methylene chloride at such a rate to maintain the reaction temperature at 0° C. After addition, the resulting mixture was stirred for 30 minutes at 0° C. Then the reaction mixture was poured into 30 ml of saturated aqueous sodium bicarbonate solution and extracted with methylene chloride. The organic extracts were dried over sodium sulfate and the solvent removed by evaporation in vacuo and thus crude 4-phenoxy-but-2-yn-1-ol methanesulfonate was obtained. The foregoing crude mesylate was dissolved in 15 ml of acetone and treated with a solution of 5.55 g of sodium iodide and 1.049 g of sodium bicarbonate in 30 ml of acetone. The reaction mixture was stirred for 1 hour at room temperature and then the solvent was removed under reduced pressure. The residue was diluted with water (25 ml) and extracted with methylene chloride, (3×30 ml) the organic extracts were dried and the solvent removed by evaporation. The residue was purified by silica gelcolumn chromatography (50 g) using hexane:ethyl acetate (95:5) as eluant, to yield 2.3 g (62%) of 1-iodo-4-phenoxybut-2-yne. The product was stored in the refrigerator.

1. additionAfter addition
2. extractionextracted with methylene chloride
3. dry with materialThe organic extracts were dried over sodium sulfate
4. customthe solvent removed by evaporation in vacuo
5. customthus crude 4-phenoxy-but-2-yn-1-ol methanesulfonate was obtained
6. stirringThe reaction mixture was stirred for 1 hour at room temperature
7. customthe solvent was removed under reduced pressure
8. additionThe residue was diluted with water (25 ml)
9. extractionextracted with methylene chloride, (3×30 ml) the organic extracts
10. customwere dried
11. customthe solvent removed by evaporation
12. customThe residue was purified by silica gelcolumn chromatography (50 g)